Chief Pilots & Aircraft Owners

A good relationship’s required between the two principal people in a flight department.

Bill Cook and Bob Harbstreit
Principal Bill Cook (left) and chief pilot Bob Harbstreit continued their close collaboration when outside the cockpit.Courtesy John King

The relationship between the chief pilot and the principal is extraordinary. Like our entrepreneur friend, Bill Cook, and his chief pilot, Bob Harbstreit, people in this relationship become mutually entwined. They develop very respectful and trusting relationships. I know of no parallel relationship outside of aviation.

It is not unusual for entrepreneurs to fly as crewmembers in their company airplanes. When that happens, it can intensify the relationship with the chief pilot. We know one entrepreneur who regularly flies intercontinentally with his chief pilot. It means they work hard and handle stress together. They are like war buddies.

But what does the chief pilot do if the principal who flies as a crewmember gets in too much of a hurry or cuts corners? One chief pilot reported that while he was still inside the FBO paying the fuel bill, the principal would strap into his pilot seat and start the engines. The chief pilot would run to the airplane, receipt in hand, clamber into the cockpit and ask, “Have you got the ATIS and clearance?” And the principal would reply: “No. Come on, let’s go.”

Bill had a Mooney when we first met him. Flying was very important to him, as it was to us. It gave us a tie with Bill that will last for the rest of our lives. Even though he became the wealthiest man in the state with lots other interests, we always had mutually engaging things to talk about.

When we meet entrepreneurs who fly, it often prompts us to wonder whether those with a passion for flying are successful because they have lots of interests or whether they can pursue lots of interests because they are successful.

As with many people who become captivated by flying, Bill’s deep interest in flying was part of a personality pattern that goes along with a habit of anticipating events and making things run well. As personality types, you can say pilots tend to be pilots in command rather than passengers throughout their lives.

Bill’s company manufactured medical devices, including, among other things, cardiovascular catheters, needles and wire guides. As the ­business grew, in rapid succession, he quickly upgraded his company airplane from the Mooney to a Cessna Skymaster, a Conquest, a Westwind II, an Astra and then a Challenger.

Although Bill employed corporate pilots, he always considered himself a crewmember and flew side by side with his chief pilot, Bob Harbstreit. Every pilot will understand why, to Bill, it always seemed such a waste to own a jet and ride in the back of it.

Bill always appreciated the knowledgeable management of the fleet by Bob and treated him respectfully, often taking him into meetings on trips with him. In one meeting of company heads, when told that Bob would have to leave when the meeting started, Bill replied, “If Bob leaves, I leave.” Bill had a deep trust in Bob’s ability to judge character and felt that he benefited greatly from it. Plus, Bob took great notes. Bill would rely on Bob for details of the meeting afterward. As the years passed, Martha and I got to know and become friends with Bob during Bill’s visits. We shared Bill’s high opinion of Bob.

To Bill, airplanes provided true mobility—a lifestyle with command of time and place. Bill could travel ­wherever and whenever he wanted.

But beyond the passion and ­lifestyle, Bill found that airplanes were powerful tools to make good things happen. Many of the company’s sales calls were by airplane; he provided his salespeople with airplanes and often flew to join them on sales calls. It enabled his business to grow to a worldwide scale. Bill called his ­airplanes his “weapons.”

Bill had as many as five ­company airplanes at one time, including BAC 111s and Boeing 727s. If they had a new product idea or a problem in the field anywhere in the ­country, they could be there and working on it the same day. With the ­airplanes, they could bring customers and technicians together in the field on short notice to create new ­products for new solutions.

Bill had a boundless habit of ­having a lot of passions and following them. Flying allowed that to ­happen. Moreover, it allowed him to ­support very special causes with aerial ­transportation—such as a ­marching drum-and-bugle corps that had been so helpful to his son. He even flew them to London where they put on an award-winning show.

If there are outside stockholders, the board often must come to terms with the concept of financially supporting the airplane for the ­benefit of a singular superstar principal. Can one person be worth a huge multiple of an average worker to the company? Can the airplane make all that much difference?

Even if the principal is not a pilot, the airplane can be the lifeblood of both the principal and the company. It is not just that the airplane is more efficient. It is that the entrepreneurial superstars of the world need and merit that flexibility. And travel is often so necessary to the way the ­company does business that these entrepreneurs aren’t willing to do it as required if it means much of their lives would be consumed in crowded airline terminals and cabins.


Read More from John King: Sky Kings


When it comes to the Bill Cooks of the world, the airplane can, for sure, make that much difference. Without it, these entrepreneurs wouldn’t be motivated to continue the work that had created the company and thousands of jobs. The fate of the company and its jobs literally hinge on the continued work of that superstar. The airplane is a very integral part of the lives of these superstars. It has been important to them since their own Mooney-equivalent days.

For both flying principals and ­nonflying principals alike, the chief pilot plays a profound role in their lives. For each of them, the chief pilot is the key to providing the true command of time and place that has come to mean so much to them.

In the process, the chief pilot gains an intimacy regarding the comings and goings of the principal and inevitably knows more about tastes and preferences of the principal than almost anyone else.

Ever since Gayle, Bill’s wife, was kidnapped for ransom, security has loomed as an issue for the Cook family, including in airplane operations. For some, such as the Cooks, the chief pilot also manages the ­mobility and freedom of movement to ­provide the personal security that cannot be assured otherwise.

Donald Trump had just such a ­person who was in charge of his mobility for both airplanes and helicopters—before he became president and incurred the resultant downgrade in personal freedom and mobility.

The close relationship between the chief pilot and the principal is a very quiet, yet pervasive one in business aviation. I often wonder whether Martha and I have such a relationship, but I can never figure out which one would be the chief pilot and which one would be the principal.